33062-26-9Relevant articles and documents
SYNTHESES OF (+/-)-CLAVICIPITIC ACID AND ITS DERIVATIVES
Somei, Masanori,Hamamoto, Shoichi,Nakagawa, Kyoko,Yamada, Fumio,Ohta, Toshiharu
, p. 719 - 724 (1994)
A formal total synthesis of (+/-)-clavicipitic acid was achieved in five steps from indole-3-carboxaldehyde.Syntheses of (+/-)-4-cyano-, (+/-)-4-methyl-, and (+/-)-4-hydroxymethyl-6-(2-methyl-1-propen-1-yl)-3,4,5,6-tetrahydro-1H-azepinoindoles are also reported.
Total Synthesis of the Clavicipitic Acids by an Intramolecular Azide Cycloaddition Strategy
Kozikowski, P.,Greco, Michael N.
, p. 2310 - 2314 (1984)
A straightforward total synthesis approach to the structurally unique ergot derailment products, the clavicipitic acids 1 and 2, is described.The synthetic strategy is based on the formation of the seven-membered nitrogen-containing ring of 1 and 2 through an intramolecular azide cycloaddition process.The cycloaddition strategy, which produces solely the imine product 24, does in some sense mimic the proposed biosynthetic pathway to these acids.
Total Synthesis of (-)-Clavicipitic Acid via γ,γ-Dimethylallyltryptophan (DMAT) and Chemoselective C-H Hydroxylation
Bartoccini, Francesca,Venturi, Silvia,Retini, Michele,Mari, Michele,Piersanti, Giovanni
, p. 8027 - 8034 (2019/06/17)
The first total synthesis of natural (-)-clavicipitic acid from ?,?-dimethylallyltryptophan (DMAT), its biosynthetic precursor, is described. This is done by regio- and chemoselective, remote, nondirected C(sp3)-H hydroxylation followed by amin
Total synthesis of clavicipitic acid and aurantioclavine: Stereochemistry of clavicipitic acid revisited
Xu, Zhengren,Hu, Weimin,Liu, Qiang,Zhang, Lihe,Jia, Yanxing
scheme or table, p. 7626 - 7635 (2011/02/25)
The stereocontrolled total synthesis of clavicipitic acid and aurantioclavine from a common azepino[5,4,3-cd]-indole intermediate is reported. This key azepinoindole nucleus was constructed via a one-pot Heck/Boc-deprotection/aminocyclization process from
